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As an unusual chemical modification to the steroid A\u2010ring could allow this compound to pass through antidoping screens undetected, the metabolism of hemapolin was investigated by an in vivo equine drug administration study coupled with GC\u2010MS analysis. Following administration of synthetically prepared hemapolin to a thoroughbred horse, madol (17\u03b1\u2010methyl\u20105\u03b1\u2010androst\u20102\u2010en\u201017\u03b2\u2010ol), reduced and dihydroxylated madol (17\u03b1\u2010methyl\u20105\u03b1\u2010androstane\u20102\u03b2,3\u03b1,17\u03b2\u2010triol), and the isomeric enone metabolites 17\u03b2\u2010hydroxy\u201017\u03b1\u2010methyl\u20105\u03b1\u2010androst\u20103\u2010en\u20102\u2010one and 17\u03b2\u2010hydroxy\u201017\u03b1\u2010methyl\u20105\u03b1\u2010androst\u20102\u2010en\u20104\u2010one, were detected and confirmed in equine urine extracts by comparison with a library of synthetically derived reference materials. A number of additional madol derivatives derived from hydroxylation, dihydroxylation, and trihydroxylation were also detected but not fully identified by this approach. A yeast cell\u2010based androgen receptor bioassay of available reference materials showed that hemapolin and many of the metabolites identified by this study were potent activators of the equine androgen receptor. This study reveals the metabolites resulting from the equine administration of the androgen hemapolin that can be incorporated into routine GC\u2010MS antidoping screening and confirmation protocols to detect the illicit use of this agent in equine sports.<\/jats:p>","DOI":"10.1002\/dta.2769","type":"journal-article","created":{"date-parts":[[2020,1,17]],"date-time":"2020-01-17T00:15:52Z","timestamp":1579220152000},"page":"752-762","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["<i>In vivo<\/i> metabolism of the designer anabolic steroid hemapolin in the thoroughbred horse"],"prefix":"10.1002","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1161-3147","authenticated-orcid":false,"given":"Christopher C.","family":"Waller","sequence":"first","affiliation":[{"name":"Research School of Chemistry Australian National University  Canberra Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sumudu A.","family":"Weththasinghe","sequence":"additional","affiliation":[{"name":"Research School of Chemistry Australian National University  Canberra Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lauren","family":"McClure","sequence":"additional","affiliation":[{"name":"Australian Racing Forensic Laboratory Racing NSW  Sydney Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3442-8617","authenticated-orcid":false,"given":"Adam T.","family":"Cawley","sequence":"additional","affiliation":[{"name":"Australian Racing Forensic Laboratory Racing NSW  Sydney Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Craig","family":"Suann","sequence":"additional","affiliation":[{"name":"Australian Racing Forensic Laboratory Racing NSW  Sydney Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emily","family":"Suann","sequence":"additional","affiliation":[{"name":"Australian Racing Forensic Laboratory Racing NSW  Sydney Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emma","family":"Sutherland","sequence":"additional","affiliation":[{"name":"Department of Physiology, School of Biomedical Sciences University of Otago  Dunedin New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elliot","family":"Cooper","sequence":"additional","affiliation":[{"name":"Department of Physiology, School of Biomedical Sciences University of Otago  Dunedin New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alison","family":"Heather","sequence":"additional","affiliation":[{"name":"Department of Physiology, School of Biomedical Sciences University of Otago  Dunedin New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2343-3226","authenticated-orcid":false,"given":"Malcolm D.","family":"McLeod","sequence":"additional","affiliation":[{"name":"Research School of Chemistry Australian National University  Canberra Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,2,4]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.722"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.1495"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.1858"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570159X13666141210224756"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1111\/andr.307"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.2112"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1080\/01961779308050628"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.1728"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac102845y"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.72"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.04.001"},{"key":"e_1_2_8_13_1","unstructured":"World Anti\u2010Doping Agency.World Anti\u2010Doping Code International Standard Prohibited List January 2019. 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